115514-29-9

Upstream product

• 1139-97-5 2,3,4,6-tetra-O-methyl-D-glucopyranose 
• 99212-20-1 (2R,3R,4R,5S,6R)-2-(acetoxymethyl)-6-phenyltetrahydro-2H-pyran-3,4,5-triyltriacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 4451-35-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl chloride 
• 591-51-5 phenyllithium 
• 51705-30-7 2,3,4,6-tetra-O-methyl-α-D-glucopyranosyl bromide 

Relevant academic research and scientific papers

Synthesis of C-Glucosides by Reactions of Glucosyl Halides with Organocuprates.

Lithium dimethylcuprate reacts with trans-2-chloro-6-methyltetrahydropyran (1) via nucleophilic substitution predominantly with inversion of configuration to afford cis-2,6-dimethyltetrahydropyran (2).Similarly, lithium dialkylcuprates displace protected α-glucosyl bromides (5) with inversion to afford the β-C-glucosides, β-1-alkyl-1,5-anhydroglucitols (6).In contrast, Grignard reagents gave mixtures of α- and β- glucosides 6 and 7, while organolithium reagents gave only elimination to 9.